Azo dyestuffs



Patented Apr. 26, 1932 UNITED STATES HERMANN WAGNER, OF BAD SODEN, GERMANY, OTTO HOCHST-ON-THE-MAIN, GERMANY, BY ADELE PATENT OFFICE.

sonsr, DECEASED, LATE or sons'r, ADMINISTRATRIX, or noons'r- WILHELM SCHUMACHER, OF SOSSENI-IIEIM, ANILINE WORKS, INCL, 035 NEW YORK, N. Y., A

GERMANY, ASSIGNORS T0 GENERAL CORPORATION OF DELAWARE No Drawing. Application filed March 15, 1928, Serial No. 262,036, and in Germany March 29, 1927.

NHz

wherein Hlg represents a halogen atom and coupling the diazo-compound with an arylamide of 2-hydroxynaphthalene-8-carboxylic acid. The dyestuffs thus obtainable are remarkable for the beautiful tints they yield and their great fastness to kier-boiling and light.

The examples hereafter given serve to illustrate our invention, but they are not intended to limit it thereto; the method of dyeing being as follows:

50 grams of boiled-off yarn are treated as regards Examples 1 and 2 for one minute, in the respective grounding liquor, well hydroextracted by centrifugating and squeezing and then dyed for half an hour in the respective dye-bath. The material is then rinsed, soaped at boiling temperature with 2 grams of soap and 3 grams of sodium carbonate per liter and then again rinsed and dried.

Ewample J.The yarn is treated with agrounding liquor prepared in the following manner:

8 grams of 2.3-hydroxynaphthoic acid-5- chlor-2-toluidide are dissolved in 500 cc. of boilin water with addition of 16 cc. of Turkey-red oil (50% strength) and 16 cc. of caustic soda solution of 34 B. The whole, after being cooled to nearly 50 C., is mixed with 8 cc. of formaldehyde of 30% strength, and made up with water to one liter. The

material is impregnated with this'liquor and then coupled with a diazo solution prepared in the following manner:

3.55 grams of 2.3-dichlor-l-amino-1- methylbenzene are mixed and stirred with 5.2 cc. of hpdrochloric acid of 22 B. and some ice-cold Water and there are then added 1.44 grams of sodium nitrite dissolved in water. After the mixture. has thus been diazotized, it is made up with cold water to one liter and the mineral acid is neutralized by means of sodium acetate.

The dyeing produced according to the above method is of a vivid bluish-red shade and of good fastness to kier-boiling and light. The dyestufi has the formula:

with 8 cc. of formaldehyde of 30% strength 1' and made up with water to one liter. The material is impregnated with this liquor'and then coupled with a diazo solution prepared in the following manner:

3.55 grams of 2.3-dichlor-4l-amino-1- methylbenzene are/mixed and stirred with 5.2 cc. of hydrochloric acid of 22 B. and some ice-cold waterand there are then added 1.44 grams of sodium nitrate dissolved in water. After themixture has thus been di- The following table shows the shades which are produced by some other dyestuffs ofthe new type it does however not embrace the whole number of-dyestuffs obtainable according to our invention:

2.8-diehlor-4-amino1- methylbenzene 2 .3 dich1or-4-amin0-1- metliylbenzene 2.3-diehlor-4-amino4- methylbenzene 2.3-(llch1or-l-amlno-1- methylhcnzenc 2.3-dichlor-4-amino-1- methylbenzene 2.3-dichlor-4-nmino-1- methylbenzene 2:3-dich1or-4-amino-1- methylbenzene 2.3dichlor-4 amino-lm'ethylbenzene 2.3-(lich1or-4-amino-1- mcthylbenzene 2.3dich1or-4 amino-1- methylbenzene 2.3-dichlor-4-amlno1- methylbenzene 2.3-hydroxynaphthoic acidanil' e 2.3-hydroxynapl1thoic acidp-to1uidide 2.3-hydroxynaphthoic acid o-chloranilicle 2.3-hydroxynaphthoic acidm-nitranilide 2.3-l1ydrpirynaphthoic acid- 0-x1n1s1d1de 2.3-hyllroxynaphthoic acidp-anisidide 2.3-hydroxynaphtholc acido-phenerldide 2.3-hyflroxynuphthoic acidm-phenetidide 2.3-hydroxynaphthoic acid 4chlor-2-anisidide 2.3-hydroxynaphtl1oic acid- 2.5-(limethoxyanilide 2.3-hydroxynaphthoic acid- B-naphthalide Bln i shred Y e110 wish red Deep red Red B 111 i shred Deep red C l e a r scarlet C l c a 1' scarlet red Deep red Claretred Wine red We claim v 1. As a new product, the compound of the following formula:

OCH;

(H OMHC said compound giving a pure Turkey-red dyeing of very good fastness to light and to kier boiling.

2. As new products the compounds of the following general formula:

' Hlg Hlg it I I===N wherein Hlg represents a halogen atom and R stands for a phenyl or naphthyl residue which may be substituted by alkyl alkoxy or halogen said compounds giving dyeings of a bluish-red tint of good fastness to light and to bucking.

3. As new products the compounds of the following general formula:

wherein R stands for a phenyl or naphthyl residue which may be substituted by alkyl, alkoxy or halogen, said compounds giving dyeings of a bluish-red tint of good fastness to light and to bucking.

4. As new products the compounds of the following general formula:

wherein one X represents chlorine, the other X stands for hydrogen, the said compounds giving dyeings of a bluish-red tint of good fastness to light and to bucking.

5. As a new product, the compound of the following formula:

OH; gel I 01 N=N I OOH3 H O-NHO-Cl said compound giving a pure bluish Turkeyred dyeing of very good fastness to light and to kier-boiling.

In testimony whereof we afiix our signatures.

HERMANN lVAGNER. ADELE SOHST, Administratrim of Otto Sohst, Deceased.

CARL SIEB. WILHELM SCHUMACHER. 

